Fifty Shades of Play
A dame that knows the ropes isn’t likely to get tied up.
—MAE WEST
HE WAS THE UGLIEST MAN I’d seen in a while. Bad teeth. Fat. Bald. Not at all the image of what my friends imagined I’d find desirable. At first glance he repulsed me. As did his atrocious grammar, stunning narcissism, and cocky demeanor, which were laughable.
But then something happened that turned my repulsion to attraction, my disgust to lust.
I was seated beside him at a dinner when he suddenly, boldly and unexpectedly, grabbed and squeezed my leg under the table.
His wife was seated across from us, which no doubt added to his thrill.
Here I was, a fiercely independent woman who’d loved and lost and loved again. I’d built a dazzling company, had beautiful, bright, loving children, an array of scintillating friends worldwide, and a bank account with enough fuck-you money to last a lifetime.
I had no time for romance, no interest in marriage, and a hot affair was the last thing on my mind.
He pursued me with a vengeance. He was powerful, too, and had his aides deliver a seemingly never-ending array of gifts: thousands of long-stemmed red roses, endless lingerie, and a life-sized stuffed lion with a motion detector that groaned and roared in his voice when I walked by. He even sent an Audi in my favorite color and a laptop fully loaded with erotic photos of a stunning twelve-inch cock attached to a hand masturbating it.
With each gesture I was repulsed and shocked and more and more titillated. It had been years since I felt so pursued. And despite all of his negatives, his allure was electric. He wanted to possess me, to own me, to make me his. For weeks he’d call at 1:00 A.M. and in his lowest, deepest voice he’d speak of the one thing every woman loves to hear: his desire for me.
I loved it. I wanted it. I fully imagined each and every cruel thing he said he wanted to do to me. He would make me beg for his cock, make me watch while other women prepped it for me. He would teach me to worship it, to run for it, to kill for it. He would handcuff me while he placed the large fat tip in my mouth and force me to sit still while he masturbated and poured his come down my throat, he would force me to put two fat dildos in my cunt while he pumped his throbbing meat into my ass. He would instruct me to lick the dicks of all of his friends under a table while they played cards, after which they would gangbang me.
I was his, and I would be his whore. When he called I would run. I would do as told. He would have me open my blouse while driving and expose my tits. I would have implants to make them huge for his pleasure. I would bring him women as toys, and I would hold their tits up for his sucking pleasure. I would lick them to prepare their juicy cunts for his hot cock. And if I pleased him, he would reward me with Take 3, his code word for one in each hole. In these late-night calls he reminded me again and again that I was his, that he would possess and control and own me, and that if I ever tried to leave him, he would kill me.
I started to believe him.
And as any forty-six-year-old woman with years of experience and a log full of memories of men would do, I agreed to meet him.
In a hotel room. Of his choosing. At his expense.
We set the time. One of his aides would arrive in advance and deliver the key to me after checking us in under an anonymous name. He was famous and didn’t want to get caught.
The suite was huge. I was to arrive thirty minutes before him. He was military precise in his plans and maneuvers. Everything down to the second.
I was waxed and buffed and polished with new pearly white veneers, freshly covered grays, highlights, lowlights, brows shaped, seven pounds lighter, firmed up, semi-permanent lashes, stunning mouthwash, seven-inch Christian Louboutins, a black lace push-up bra peeking through my hot pink satin blouse and a desire that burned inside me in a way I’d never known.
After setting out my toys and gadgets (he’d had one of his aides hand-deliver the list) I sat on the plush, teal velvet couch in this massive suite, my leg bobbing nervously, freshly doused in Déclaration, his favorite Cartier perfume.
I was nervous, thrilled, excited, and ready. Loaded, cocked, and ready.
Thirty minutes passed. Then forty-five. Fifty. Sixty. For a man with a fierce dedication to detail, this was another surprise. I called his cell. No answer. I called his cell again. No answer. I called his cell a third time. It was off.
Was this to show me that he owned me? That my time was his? That I would wait? That he could keep me waiting? With each passing minute I grew more anxious. Should I leave? Had something happened to him?
He arrived eighty-two minutes late. He announced it as he came in, tore off his clothes, and jumped in the shower.
“I ran into Anna Kournikova at the airport. Her driver was late so I gave her a ride into the city. She invited me in. I didn’t have time to call you,” he said as he walked out of the bathroom soaking wet.
I was to wait. I was to submit. To accept. To take his crumbs. To honor his every move. Every word. I was to stroke his ego, to open myself up to any and all of his desires. I was to sit at his feet awaiting his next order, ready to serve, and be thrilled for the asking.
He pulled a whip and handcuffs out of his bag and threw me on the bed.
He placed the handcuffs beside me.
I told him I was nervous. I needed a drink to relax. I asked his permission. I begged him to join me in a toast to his cock.
I poured the champagne. We clicked. Sipped. Then gulped.
Within minutes he was drowsy and barely able to move. The drug worked quickly as promised. He collapsed on the bed and I quickly handcuffed him to the bedposts.
He was having a hard time comprehending what was happening but I lifted his knees to his chest, strapped a double dick strap-on to my waist, and told him to beg for more as I penetrated his eager ass.
He didn’t know what he was saying, but I fed him line after line.
SAY IT!
I worship your dick.
Fuck my ass.
Rape my ass.
I am a cock lover.
I want to be fucked.
I am your cock slave.
Finally, I shoved a large, thick, black glass dildo into his mouth, two in his ass, and said, “TAKE 3, MOTHERFUCKER.”
He passed out after that. I collected my things, including the hidden camera I’d installed in the room, turned on the iPod player on which I had downloaded our tape-recorded phone conversations, and pumped up the volume. I wanted him to hear it as his wake-up call.
Mae West said it best: “A dame that knows the ropes isn’t likely to get tied up.”
JUDITH REGAN is a publisher, talk-show host, and producer. She hosts The Judith Regan Show on the SiriusXM Stars Channel.